Hydroxyorganosilanes



United States Patent 3,355,473 HYDROXYORGANOSILANES Harold A. Clark and Loren A. Haluska, Midland, Mich., assignors to Dow Corning Corporation, Midland, Mich., a corporation of Michigan No Drawing. Original application Apr. 1, 1963, Ser. No. 269,781, now Patent No. 3,317,460, dated May 2, 1967. Divided and this application Dec. 21, 1966, Ser. No.

9 Claims. (Cl. 260-4482) 1 or 2, c is 2 or 3, and all of the hydroxyl groups are primary hydroxyl groups, are claimed.

This application is a division of our application Ser. No. 269,781, filed April 1, 1963, which is now U.S. Patent No. 3,317,460.

This invention relates to new silanes.

The silanes of this invention are useful as curing agents for isocyanate prepolymers, for preparing polyurethane rubbers and for making varnishes.

This invention also relates to silanes of the general formula [(HO) R] SiR' wherein R is a trivalent or tetravalent hydrocarbon or hydrocarbon ether radical bonded to the silicon atom via a silicon carbon bond, R is a monovalent hydrocarbon radical free of aliphatic unsaturation, a is 2 to 3, b is 1 or 2, c is 2 or 3, and all of the hydroxyl groups are primary hydroxyl groups. It is obvious, of course, that the sum of a-ib must be equal to 4.

In the above formulae, for example, the [(HO) R] group can be, for example, aliphatic radicals such as (HOCH CHCH CH (HOCH CH (HOCH )CHCH CH CH CH (HOCH CH CCH CH (HOCH CH (HOCH CHCH(CH OH) CH CH CH HOCH CH CH CH CH CH CH CH OH) CH CH CH (CH CH HO CH CH CHCH CH (HOCH CHOCH CH CH (HO CH CHOCH CH (HOCHz) (HOCH CH CH CH )CHOCH CH CH (HOCH CH CHCH OCH CH CH or a (HOCH C (CH [CH (OCH CH OCH CH CH group and cyclic radicals such as (HOCH2)2C(CH3) on,o@cnzcni- (nocnmo (011.) CH2O $011,011?

In the above formulae the R groups can be, for example, alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, hexyl, heptyl, octyl, nonyl,

decyl, dodecyl, pentadecyl, octadecyl; cyclic hydrocarbon groups such as phenyl, tolyl, benzyl, xenyl, naththyl or a cyclohexyl group.

The silanes of this invention can be prepared by any suitable process such as by the addition of the appropriate hydroxy oiefinic compound to the appropriate silane containing one or two silicon-bonded hydrogen atoms per silicon atom in the presence of a platinum catalyst. This and other suitable processes by which these silanes can be prepared are well known and will be obvious to those skilled in the art. Illustrative of these processes is the one d sclosed in U.S. Patent 2,823,218.

In order that those skilled in the art may better understand how the present invention can be practiced, the following examples are given by way of illustration and not by way of limitation.

Example 1 A mixture of 174 g. of trimethylolpropanemonoallylether and 20 drops of a .1 M chloroplatinic acid solution in butyl acetate was prepared and heated to C. Then 61 g. of phenylmethylsilane was added slowly over a period of about 18 minutes. The reaction was very exothermic so the mixture was externally cooled during the addition to keep the temperature of the mixture in the range from -130 C. A grey solution of low viscosity which was a silane of the formula below was obtained.

OHzOH CaH CHQOH CHzCHzC-CHgO (OH2)aSi(CHa)3O CH2-C CHzCHa CHzOH CH3 CHzOH Example 2 When stoichiometric amounts of the following silanes and hydroxy olefinic compounds are reacted employing the process of Example 1, the indicated product is obtained.

A C6H5 2SlH2 Olefin(HOCI-I CCH OCH CH CH Product( C H Si[ (CH OCH C CH OH) 2 silane-(CH 2(C3H7) Olefin( HOCH CH CH J CHO CH OCH CHiH Product C Silane(CI-I 2SIH2 OIefin-(I-IOCH CH CCH=CH Product-(CH Si [CH CH C (CH CH OH) 3 2 That which is claimed is: 1. A silane having the general formula I: c b a.

wherein each R is independently selected from the group consisting of trivalent and tetravalent hydrocarbon and hydrocarbon radical free of aliphatic unsaturation, a is atom through a silicon-carbon bond, R is a monovalent hydrocarbon radical free of aliphatic unsaturation, a is an integer from 2 to 3 inclusive, 'b is an integer from 1 to 2 inclusive, the sum of a and b being 4, c is an integer from 2 to 3 inclusive, 0 being 2 when R is trivalent and 0 being 3 when R is tetravelent, and all of the hydroxyl groups are primary hydroxyl groups.

2. A silane as defined in claim 1 having the general formula CH O 3 SiR' 3. A silane as defined in claim 2 wherein b is 1.

4. A silane as defined in claim 2 wherein b is 2.

3 4 5. A silane as defined in claim 1 having the general References Cited formula 6. A silane as defined in claim 5 wherein b is 1. 7. A silane as defined in claim 5 wherein b is 2. 2,629,727 2/1953 Spelel' 260-41482 8. A silane as defined in claim 4 having the formula 5 [CHBCHZC(CHZOH) 2CH2O(CH2)3] 2si(C6H5)2' TOBIAS E. LEVOW, Prlmary Examiner.

9. A silane as defined in claim 4 having the formula I, P, PODGORSKI, Examiner, [CH H2 z zc z 2) 3] z s s) 2- UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,355,473 November 28, 1967 Harold A. Clark et al.

It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 2, line 61, beginning with "radical free" strike out'all' to and including "hydroxyl groups." in line 68 same column 2, and insert instead ether radicals and is bonded to the silicon atom through a silicon-carbon bond, Ris a monovalent hydrocarbon radical free of aliphatic unsaturation, a is an integer from 2 to 3 inclusive, b is an integer from 1 to 2 inclusive, the sum of a and b being 4, c is an integer from 2 to 3 inclusive, c being 2 when R is trivalent and c being 3 when R is tetravalent, and all of the hydroxyl groups are primary hydroxyl groups column 3 li 6 for "[CH CH C(CH OH) CH O(CH 1 8i (C H read Signed and sealed this 13th day of May 1969.

EDWARD M.FLETCHER,JR. Attesting Officer Commissioner of Pat ts (SEAL) Attest: 

1. A SILANE HAVING THE GENERAL FORMULA 